When should I just give up?

So, another of my somewhat secret, no longer so secret predilections: I love me some advice columns. Any old advice column will do - Dear Abby (though she frequently ruffles my feminist feathers), Dear Prudence (though she too gets under my skin with her frequent Emily Post referrals), Cary Tennis anachronistic Since You Asked column at Salon, Dan Savage and his delightful neologisms on Savage